1992Mark Wahlberg drops trou for Calvin Klein revealing his affinity for sexy boxer briefs and further cementing popularity and longevity for the new underwear style.

2000Underwear shopping gets much more convenient with online shopping at Freshpair.com. Free domestic shipping, saving gas money, and avoiding department store crowds make the shopping experience so much more pleasant.

3000 B.C.ELeather loincloths are both functional and stylish.

1300Braies replace the loincloth as a predecessor to baggy boxer shorts. Primitive in design, the braie features a loose fit and a drop-crotch.

1793The cotton gin is introduced and is a pivotal moment in underwear history. Mass-produced cotton underwear soon hits shelves.

1911J.C. Leyendecker illustrates the first national advertisements for men’s underwear. Newspaper subscribers are scandalized and tantalized.

1934The fly-front is invented creating easy access for right-handers.

1936Munsingwear designs “kangaroo pouch” horizontal fly underwear for men. Finally, a fly-front that works for left-handers!

1950Innovations in color, pattern, and design lead the way in fashion underwear for men.